


Late Night Session

by assbuttintheimpala



Series: A Summer Affair [3]
Category: Supernatural
Genre: Alternate Universe - College/University, Alternate Universe - Human, Feminization, Infidelity, M/M, Masturbation, Phone Sex, Sex Toys, Size Kink
Language: English
Status: Completed
Published: 2013-06-13
Updated: 2013-06-13
Packaged: 2017-12-14 20:54:27
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,439
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/841277
Author URL: https://archiveofourown.org/users/assbuttintheimpala/pseuds/assbuttintheimpala
Summary: <blockquote class="userstuff">
              <p>It was one night while Castiel entertained himself that he had an idea. His mind was full of pictures of Dean as he pleasured himself. He had his biggest dildo shoved up his ass and it wasn’t nearly enough.</p>
            </blockquote>





	Late Night Session

**Author's Note:**

  * Translation into 中文 available: [Late Night Session 夜谈](https://archiveofourown.org/works/5420948) by [destielarmyCN](https://archiveofourown.org/users/destielarmyCN/pseuds/destielarmyCN)



> This wasn't meant to be more than a one shot. Damn you all and your insistence :P

Castiel once again hadn’t seen Dean for a few weeks. Dean had told Castiel he would be busy at work for the next while and they wouldn’t be able to do anything until things calmed down a bit at the auto-shop. Of course, that left Castiel disappointed but he had managed to score Dean’s number which had perked his mood.

Things around the house improved as Anna returned to work. It became a lot easier for Castiel to avoid her and any awkward meetings. He found that if he slept in till Anna left for work and then found his way back into the house before Anna got home, which was usually quite late, he avoided seeing her all together. The only time they would tend to have to interact was when they were with their younger siblings.

Castiel took it upon himself to entertain them while it was still hot outside and would usually take them to the park to throw a ball around and have a picnic before they would return home and take a dip in the pool. Castiel loved spending time with his siblings and he knew when he left for college, he was definitely going to miss them.

During the week, Castiel looked after the kids while everyone else was at work and their nanny was on a break and then on the weekend Anna would take over. Sometimes she would ask Castiel to join her which he did so reluctantly and then spent the entire time with everyone but Anna. He knew he was being suspicious but it was better than having to lie through his teeth about why he couldn’t look her in the eye.

With Castiel having to look after the children, he found hardly any time to himself and it got harder and harder to not just call Dean and demand him to meet Castiel so they could fuck. But, Dean was busy and that left Castiel to have to make do with what he had. It was never enough but it gave him a little satisfaction until he could meet up with Dean again.

It was one night while Castiel entertained himself that he had an idea. His mind was full of pictures of Dean as he pleasured himself. He had his biggest dildo shoved up his ass and it wasn’t nearly enough. His back was arched off the bed with his head pushed back into the pillows and his feet firmly placed on the mattress as he pumped the device in and out of his hole as he tried to get himself off. Frustration had sunk in as he wasn’t nearly stretched wide enough nor full enough for the way he liked it since Dean. As the need to get off became more and more of a necessity than a luxury, Castiel moved the hand that was currently wrapped around his dick to his entrance.

They were slick from the precum that was smeared all over his cock as he jacked himself off so there was no need to stop and find the lube. He stopped his thrust of the toy as he carefully slipped another finger inside himself. He groaned as he felt himself stretch wider. Simultaneously, he pumped the toy and his finger before he was stretched enough to add another.

When the second slipped in, he started to feel that burn that he got with Dean. He fucked himself down hard onto the toy and his fingers to try and get towards the edge. He added and third and he nearly lost it. He had it. He had the stretch and the burn that came when Dean fucked into him and never wanted to lose it. He imagined Dean hovered over the top of him as he thrust into Castiel’s body unrelenting with his power. It was then that his brain reminded him that he had Dean’s number.

It was a Thursday night and he knew Dean would have work in the morning but he wanted to show Dean just how much he wanted him to come and fuck him again. With his fingers and toy still in his ass, he turned his head to try and find where he had placed his phone. He spied the device on his bedside dresser and groaned in annoyance at how far away it was but the potential of what he was going to do was too great to ignore.

Grudgingly, Castiel let his hand that pumped the dildo into his ass release the device and reached for his phone. As he went, he wiped his hand free of the lube onto his comforter so he didn’t get it all over his phone and probably drop it due to the slipperiness. That would just be an inconvenience to everyone involved if that happened. Once his hand was as clean as it was going to get without actually washing it, he picked up his phone and quickly activated the camera.

He wanted to get a full body shot that would show exactly what he was doing to himself as well as show his arousal along with his face. He didn’t want it to be an anonymous photo he wanted it to be personalised for Dean. Realisation dawned on Castiel as he realised that wouldn’t be possible by himself. He would need to either get someone to take it or set the device up somewhere so he could set the timer and position himself for it. With the first option out the window, Castiel looked around his room for somewhere to put his phone.

His dresser across the room would be a good spot but it would give an odd angle and he wanted it to be more of a shot that looked up his body. His desk was out of the question as it was too far away from the bed and Dean wouldn’t be able to see anything. Suddenly, Castiel thought of the perfect spot to set up his phone. He quickly turned around to face the headboard, reluctantly removing his fingers from his ass but kept the toy firmly in place, and sat up on his knees. He opened the options on his phone to set the timer for two minutes which would give him enough time to position and start to pleasure himself again which would give the photo a more authentic aspect. With one last option left, he set the camera to take multiple shots so he would have a few to choose from in case some didn’t work out.

With the camera in place on the headboard, Castiel lay himself back down onto the bed. He brought a couple of pillows with him so he could prop his head up and look at the camera while he did so. So Dean would get a great view of exactly what Castiel did to himself, he spread as legs as wide as he could and raised his ass in the air which gave the camera the best view it was going to get of his entrance. As the headboard was raised a bit above the bed, Castiel knew his whole body would still be in the shot which meant that his leaking erection as well as his face would be in it.

Once he was positioned, he figured he had about half a minute before the camera would begin to take photos. He quickly gave himself a few lazy strokes while he moved his hand back down to his hole and slid one finger back in before he gradually built up to three in his ass. His fingers were in place as he pumped the dildo once more in and out repetitively.

Castiel’s head pushed back into the pillows in pleasure as he fucked himself once again. He heard the camera shutter sound and remembered that he was taking photos of himself. He was so caught up in the burn and pleasure of having his ass full again that he had forgotten what he was in the process of. Hurriedly, he lifted his head and looked up at the camera with half-lidded eyes barely able to keep them open so he could give Dean a good shot.

To hold back the groans and keens that begged to escape, he bit down hard on his lip and kept his relentless ministrations going before he struck his prostate. He arched off the bed in a silent cry as the pleasure shook his body before he flopped back down. A few moments and strikes to his prostate later, Castiel became aware that the camera had stopped taking photos. He didn’t want to stop but at the same time he really wanted to send the photo to Dean while he was still going at it just so in case Dean was in the mood to reply, he would still be able to get off with him.

With every inch of self-control he possessed, Castiel once again removed his fingers and let go of the toy. He lay still for a moment once he had stopped his thrusts to compose himself before he rose to his knees while he clenched around the toy and reached for his phone. Again he had to wipe his hand free of the gunk on his hand so he could get a firm grasp on his phone.

His hand shook from pleasure and a small amount of nerves as he picked it up and looked through the photos. Some of them were blurry as he was mid-movement when the shutter had gone off but the majority of them were pretty good quality. As he scrolled, he bookmarked the ones that he thought were good enough to send to Dean and put them in a separate folder. When he reached the end, he opened the folder and looked through them again.

After much debate, Castiel finally decided on two photos. The first had Castiel looking at the camera with half-lidded eyes with his teeth sunk into his bottom lip which made him look unbelievably innocent. The second he was arched off the bed, head thrown back in ecstasy with a fresh spurt of precum spread from his cock to his stomach. His mouth was opened in a silent cry and Castiel couldn’t help but give his cock a few tugs at the view of himself. If he liked it that much, Dean would to love it.

All nerves and hesitation were thrown aside as he opened a new message to send to Dean.

**[To Dean: Wish you were here. Need something bigger]**

He typed out the message and attached the two photos. Before he sent it, he triple checked that he was indeed sending it to Dean and not anyone else. Once he was assured of the recipient, he pressed send and fell back down onto the bed. He would wait a few moments to see if Dean would reply before he pleased himself again. If Dean didn’t reply, he’d just keep going till he got off and if Dean did, well they would go from there.

A few minutes passed and there was no reply from Dean. Castiel had given himself a few lazy strokes in the time that he waited to keep his arousal in check while he thought over what would happen if Dean replied.

He sighed as he realised that all hope was lost and Dean was not going to reply. Thoughts flooded his mind that Dean was already tired of him and no longer wanted to carry on whatever this thing was that they were doing. Dean didn’t want him and he was going to have to find someone while he was at college that could give him what he wanted. The thing was he didn’t want some guy from college he wanted Dean but Dean was Anna’s even if whatever they were doing betrayed that. Dean belonged to Anna first and until and _if_ that ever broke apart, he would belong to her.

The vibration of his bed brought Castiel out of his depressed state. He thought it was just a message but soon realised it was still going which meant it was a call. He quickly moved to pick up his phone and glanced down at the screen to see Dean’s name flash across the screen with the option to answer. Dean had called him. Dean wanted to talk to him. Ecstatic, Castiel answered the phone.

“Hello Dean” Castiel answered his voice low and as sexual as he could get it.

“Damn princess, are you trying to kill me?” Dean replied which had Castiel trying to hold back a giggle. He was trying to be sexy not a teenage girl.

He composed himself quickly and spoke again with the best innocent voice he could muster “I just thought seeing you were working so hard, you could do with a little pick me up”

“Little would be an understatement. I’m hard a rock right now just looking at this photo of you princess” Dean said. His voice was thick with arousal and Castiel couldn’t hold back the groan at the image that entered his mind with what Dean said. He wanted that cock; so bad.

“I need it Dean. I need your cock” Castiel panted as he wrapped a hand around himself again. “Can’t get off without it”

His words earned a chuckle from Dean “Damn princess, you have a dirty mouth on you. But from the looks of it, you have all you need with you. Dildo and your fingers in your ass and you’re still not satisfied? You have a greedy pussy on you don’t you?”

“Mmm yes” Castiel hummed as he fucked up into his hand “Hungry for you Dean. Need it so bad. Come and fuck me Dean.”

He heard Dean release a small groan through the phone and knew the man was touching himself too. “Know I would princess but I have work in the morning. Soon princess, soon” he breathed through small keens. They were both caught up in their own pleasure to talk much more but just as Castiel started to get lost in the feelings that rushed through his body, Dean brought him back down “Does that dildo vibrate? You got it turned on?”

Castiel nodded and only realised a moment later that Dean can’t actually see him “Yes it vibrates” he keened “Not turned on”

“Turn it on princess. I want to hear your pretty little sounds” Castiel whimpered he didn’t want to turn it on. He never lasted long when he activated it and he usually liked his sessions to last but Dean wanted him to and Castiel couldn’t find it in him to deny him.

In order to free both hands, he turned the phone to speaker and placed it on his chest before he slid his hand down his chest to where the dildo was still stuck in his ass. He felt around until he found the switch and turned it on to the lowest level. When he felt the vibrations begin, he let out a small whimper that had Dean groan through the phone.

“That’s it princess” Dean groaned “All those pretty sounds just for me. Turn it on the highest”

Castiel paused unsure if he heard Dean correct. Did Dean want him to put it on the highest? God Castiel had never lasted long enough to try it. He had almost always cum before he got that high and there was no way he was going to be able to last with Dean’s voice and groans in his ears as well as the vibration inside him.

“Come on princess” Dean spoke again “Turn it up. Want to hear you scream”

“Can’t” Castiel whined “won’t last”

“Do it” Dean growled through the phone. The tone had Castiel startled for a moment before it just made him more turned on. Dean was unbelievably sexy when he was demanding.

Castiel obediently moved his hand and turned the device up to its highest level. His whole body shook from the sensation and he arched off the bed unable to keep back the loud shriek that came up his throat. He was dimly aware of his phone as it fell from his chest before he heard Dean’s voice right beside his ear.

“So good for me princess” he praised while Castiel sobbed and writhed on the bed. He was about to lose it and he knew Dean was close too if the pants in his ear were anything to go by.

“Dean” Castiel chocked “Dean… I need…”

“I know princess. Cum for me. I know you can do it. Think of me pumping my cum in your pussy. Fucking you so hard you can’t sit for days without thinking of what I did to you.”

Castiel couldn’t hold back anymore and cried out his orgasm. He coated his chest in cum as he arched off the bed. As he came down from his high, he heard Dean orgasm through the phone. The device still vibrated in his ass and he had to quickly turn it off before the sensation became too much and just began to overstimulate him. Once he heard Dean’s orgasm finish, Castiel grabbed his phone from beside his ear and activated the camera again while still in the call with Dean. With his hand raised above him, Castiel took a photo of the mess he’d made while his teeth sunk down into his bottom lip.

He turned his phone around and looked at the photo and was satisfied with the outcome. He pulled up another new message and sent the photo to Dean after he had once again triple checked he was sending it to the correct person. When he was done, he relaxed into the mattress and waited for Dean’s reaction. He heard Dean’s phone beep quietly to indicate a new message and Castiel smirked.

“Open it” he breathed his voice was wrecked from his cries and he was surprised that no one had come to check what the noise was about. If they had, Castiel would just go with his classic excuse that he was watching a horror movie and accidentally turned the volume up. It worked every time.

After a couple of seconds of a faint clinking sound as Dean opened the message, there was a loud groan which had Castiel unbelievably smug.

“You _are_ trying to kill me” Dean groaned

Castiel let out a small huff of a laugh “Where would be the fun in that? I like your cock too much to kill you” There was a lifeless laugh on the other end of the line and Castiel lay in confusion as to why Dean wasn’t more amused by the joke. Castiel was under no illusions that what he and Dean had was just sex; nothing more. Dean had his relationship with Anna and a thing on the side with Castiel. Before Castiel was aware of what he was saying, he spoke “What’s wrong?”

There was a slow exhale of breath on the other end before Dean replied “Nothing”

Castiel knew it wasn’t nothing. Something was eating away at Dean and Castiel wanted to know what it was. “No,” he said with a bit more force than intended “Tell me”

“It’s nothing. Just leave it” Dean replied “I’ll talk to you later”

“Dean wait-“ but he was gone. Dean had hung up and Castiel was left dumbfounded as to what the hell had gotten into Dean. He thought things were good between them that they were both on the same page and fully aware of what this was between them. He thought that maybe Dean was just feeling guilty about what he was doing to Anna and the guilt had just finally boiled over and he had started to take it out on Castiel. Of course, they were both equally to blame for this affair so it wasn’t fair for Dean to be angry at Castiel.

The thought of Dean being angry at him started to fuel Castiel’s own anger. Dean had no right to be pissed at Castiel. Sure he had started it by taking advantage of him while he slept but Castiel didn’t force Dean to do anything once he woke up and he sure as hell wasn’t the one who started the kiss at the store. How their whole relationship had progressed was solely based on what Dean gave out and Castiel just took what he was given. So maybe Castiel had started their latest session, but Dean was the one to pursue it. Castiel just put himself out there for the taking; he wasn’t to blame if Dean took what was there, surely?

While his thoughts ran wild, the mess on his chest had dried and had become stiff and uncomfortable. With a sigh and a slight wince, Castiel stood from his bed on shaky legs and made his way over to the adjoined bathroom. His shower was a walk in one with a glass divider that stopped the spray from coating the whole room. The shower head was also one of those detachable ones that made the job of cleaning below the waist a lot easier.

When it was up to temperature, Castiel walked in and allowed the warm water to flood over his body. The pressure was amazing and he really hoped the showers at college were decent. As his hair grew damp, Castiel pushed the excess hair from his face so that the water flowed freely over his face. He couldn’t help but let his thoughts run back to Dean and his reaction to the joke. Castiel scoffed to himself as he thought it over again. Dean was being ridiculous and as soon as he was done cleaning himself he was going to message Dean exactly that.

Castiel reached for his body wash and lathered it over his torso and dick to wash away the dried cum as well as the smell. He detached the head of the shower and moved it over his chest to get the best pressure to wash away the soap suds. When his skin was clean, he replaced the head and picked up his soap again so he could clean out his ass. He winced again as he touched his stretched rim but he needed to get rid of the lube otherwise it would just be uncomfortable later. He made quick work of it after having done this many times before.

After a few minutes, he was finally clean and he turned off the shower. He stepped out past the glass partition to get a towel of the heated towel rail and ran it through his hair to get rid of the excess water before he dried himself off a bit. When he was dry, he folded the towel and put it back in its place and walked back into his room to find a pair of boxers to wear to bed.

With his phone in hand, which gave the room its only source of light, Castiel was snuggled under the covers in the middle of his bed where he could still smell the traces of lube and cum. He would need to wash his bedding in the morning. Castiel scrolled through his contacts before he came to Dean’s name. Should he call? He needed to talk to him about this. If Dean was having guilt issues then he really should deal with it and if it needed to be done, Castiel would call whatever they were doing off and just find someone who was unattached to scratch his itch. It wasn’t something he wanted to do but if Dean needed him to do that then he would.

With one final exhale, Castiel pressed dial and called Dean. After a few rings, Dean answered.

“What do you want?” Dean asked his tone was grumpy and tired. He obviously didn’t want to speak to Castiel.

“I want to know what’s wrong” Castiel said simply. He wanted Dean to open up to him.

“What are we? What is this?” Dean said after a few moments of silence. The question took Castiel by surprise. He hadn’t expected Dean to want to label what they had together. What would Castiel label it anyway? He was Dean’s bit on the side.

“What do you mean? It’s sex, Dean. We are fucking and you’re dating my sister” Castiel answered

“What?” Dean somewhat yelled and Castiel could have sworn he heard surprise in his tone.

“We have sex. You are my sister’s boyfriend” Castiel said exasperated. He didn’t really think Dean needed Castiel to tell him this but apparently he did.

“What the fuck are you talking about? I broke up with Anna weeks ago”

Castiel was gobsmacked. He didn’t know what was happening. Did Dean really just say that or is he dreaming? Surely he’s fallen asleep and he’s just dreaming this conversation right now. With the hand that wasn’t holding the phone he moved it across to his other arm and pinched himself hard. Nope he’s not dreaming.

“What?” Castiel squeaked unable to fathom what was going on.

“I broke up with her about a week after we first did… ya know…” Dean answered his voice confused “I thought you knew that? Did she not tell you? I thought you were close?”

Castiel coughed “No… I mean yes we are close. Well we were until you fucked me then I couldn’t look her in the eye because of what we did. Are you seriously telling me right now that this whole summer I’ve been avoiding my sister because I’ve felt unbelievably guilty that I’m being fucked by her boyfriend only I’m not?”

“Uhm… yes?” Dean answered

“Fuck” Castiel sighed

“You okay there princess?” Dean asked with a chuckle which just frustrated Castiel. How could Dean be so calm about this?

“I need time to think this over, Dean. Can I talk to you tomorrow or something?” Castiel asked as he ran a hand through his damp hair. He really couldn’t believe that this was happening.

“Yeah, yeah sure. I’ll talk to you later I guess” Dean said before he said goodbye and hung up after Castiel returned his goodbye.

Castiel lay in his bed and stared at the ceiling as he mulled over what Dean had just said. Anna and Dean weren’t together. They hadn’t been for weeks. Dean was single. Dean was fucking Castiel. Castiel had been avoiding his sister out of guilt for something he shouldn’t even feel guilty for.

“Fuck” Castiel spoke to the silent room. It was going to be a long night.


End file.
